Nicotinic Acid → N-Nicotinoyltyrosine ethyl ester

HRID 1085181

Reaktionsgleichung

Reaktionsgleichung von HRID 1085181
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH2:26]([O:28][C:29](=[O:40])[C@H:30]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[NH2:31])[CH3:27]>N1C=CC=CC=1>[CH2:26]([O:28][C:29](=[O:40])[C@H:30]([CH2:32][C:33]1[CH:34]=[CH:35][C:36]([OH:39])=[CH:37][CH:38]=1)[NH:31][C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1)[CH3:27]

Komponenten

5

Edukt 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 2724939Tyrosine ethyl ester hydrochloride

Produkt 1

HCID 53849020N-Nicotinoyltyrosine ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Nicotinic acid (12.3 g, 0.1 mol) was dissolved in dry pyridine (300 ml). The solution was cooled and dicyclohexylcarbodiimide (20.6 g, 0.1 mol) was added. After dissolution, tyrosine ethyl ester hydrochloride (24.6 g, 0.1 mol) was added and the solution was stirred overnight. The precipitated dicyclohexylurea (DCU) was removed by filtration. Additional DCU was removed by triturating the oil with hot water. The product was purified with acetone. Calculated for C17H18N2O4. 1/2H2O: C, 63.16; H, 5.88; N, 8.66. Found: C, 63.10; H, 5.96; N, 8.59. The product can also be named N-[1-ethoxycarbonyl-2-(4'-hydroxyphenyl)ethyl]nicotinamide.

Aufarbeitung

  1. temperatureThe solution was cooled
  2. additionwas added
  3. customThe precipitated dicyclohexylurea (DCU) was removed by filtration
  4. customAdditional DCU was removed
  5. customby triturating the oil with hot water
  6. customThe product was purified with acetone

Quellen und Nachweise

ORD-Eintrag
ord-01b99af046de480faf89bd04e505f4fe
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05008257

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